A Simple Dialkylated Enol

Hoffmann, H. M. R.; Schmidt, E. A.

doi:10.1002/anie.197302391

Cited by 8 publications

(1 citation statement)

References 4 publications

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“…The enol content of ethanal, for example, amounts to merely 0.00006% . Nevertheless, excess concentrations of metastable enol solutions have been obtained by photoelimination , or careful hydrolyses of enol orthoesters. ,, Chin and Bosnich described elegant transition-metal-catalyzed isomerizations of allylic alcohols to enols, which are stable for minutes to hours at ambient temperature and a stable enol, 2-methyl-1-propen-1-ol, has even been obtained at low temperatures (−20 °C) . Still, simple enols remain unusual, and few NMR or reactivity studies are available.…”

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confidence: 99%

Reversible Generation of Metastable Enols in the 1,4-Addition of Thioacetic Acid to α,β-Unsaturated Carbonyl Compounds

Hintermann

Turočkin

2012

J. Org. Chem.

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Addition of thioacetic acid to reactive α,β-unsaturated carbonyl compounds like acrolein or crotonaldehyde in acetone-d(6) generates metastable (E)- and (Z)-1-alkenols, which tautomerize slowly at ambient temperature. The 1,4-addition of thioacetic acid and crotonaldehyde to (Z)-3-(acetylsulfanyl)-1-propen-1-ol is reversible with K(eq) = 5.5 ± 0.5 L/mol. A concerted, cyclic 1,4-addition mode is proposed to explain the preferred (Z)-stereoselectivity in lower polarity, nonprotic solvents.

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